Triacetoxyperiodinane → HCID 178489407, compound

HRID 2389010Notes

Reaction equation

HRID 2389010 reaction equation
[F:1][C:2]1[C:3]([NH:30][CH:31]2[CH2:36][CH2:35][CH:34]([OH:37])[CH2:33][CH2:32]2)=[C:4]([CH:10]=[C:11]([C:13]2[CH:14]=[C:15]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH3:29])=[N:20][NH:19][C:16]3=[N:17][CH:18]=2)[CH:12]=1)[C:5]([N:7]([CH3:9])[CH3:8])=[O:6].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>ClCCl>[F:1][C:2]1[C:3]([NH:30][CH:31]2[CH2:36][CH2:35][C:34](=[O:37])[CH2:33][CH2:32]2)=[C:4]([CH:10]=[C:11]([C:13]2[CH:14]=[C:15]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH3:29])=[N:20][NH:19][C:16]3=[N:17][CH:18]=2)[CH:12]=1)[C:5]([N:7]([CH3:9])[CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 178489408HCID 178489408, compound

Product 1

HCID 178489407HCID 178489407, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Fluoro-2-(4-hydroxy-cyclohexylamino)-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N,N-dimethyl-benzamide (167 mg, 0.33 mmol) and 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (212 mg, 0.5 mmol; Dess-Martin periodinane) were dissolved in 5 mL dichloromethane and stirred overnight. The reaction was quenched with a saturated sodium bicarbonate solution, applied to a Varian Chemelut cartridge and eluted with ethyl acetate. Purification by flash silica gel chromatography using a gradient of ethyl acetate and hexanes afforded 3-fluoro-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N,N-dimethyl-2-(4-oxo-cyclohexylamino)-benzamide as a white solid (113 mg, 0.23 mmol, 68%). 1H NMR (500 MHz, DMSO-d6) δ 13.78 (s, 1H), 8.82 (s, 1H), 8.30 (s, 1H), 7.63 (m, 2H), 7.45 (m, 1H), 7.34 (s, 1H), 7.20 (d, J=10 Hz, 1H), 7.08 (t, J=8 Hz, 1H), 4.80 (d, J=9 Hz, 1H), 3.82 (s, 3H), 3.71 (m, 1H), 3.01 (bs, 3H), 2.92 (bs, 3H), 2.37 (m, 2H), 2.24 (m, 2H), 2.05 (m, 2H), 1.69 (m, 2H). MS: m/z 502.2 (M+H+).

Workup

  1. customThe reaction was quenched with a saturated sodium bicarbonate solution
  2. washeluted with ethyl acetate
  3. customPurification by flash silica gel chromatography

Sources & evidence

ORD record
ord-4e7b79459a7a4fdfae6be56728c2adf9
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

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